Thermal Rearrangements

Authors

  • Prof. Dr. W. von E. Doering,

    1. Department of Chemistry, Yale University, New Haven, Conn. (U.S.A.)
    2. Institut für Organische Chemie der Universität Köln (Germany)
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    • Lecture delivered at the presentation of the August-Wilhelm-von-Hofmann-Denkmünze of the Gesellschaft Deutscher Chemiker on September 12th, 1962 in Munich.

  • Dr. W. R. Roth

    1. Department of Chemistry, Yale University, New Haven, Conn. (U.S.A.)
    2. Institut für Organische Chemie der Universität Köln (Germany)
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Abstract

The effect of conjugation with double bonds and (in cyclopropane) the effect of ring strain on the cleavage of carbon-carbon bonds during thermal rearrangements is discussed. In particular, the Cope rearrangement and the geometry of its transition state are described. The structurally degenerate Cope rearrangement of bicyclo[5. 1. 0]octa-2,5-diene is discussed, and this compound is used to illustrate the concept of “fluctional structure”, which finds its extreme expression in the hypothetical compound, tricyclo[3. 3. 2. 04,6]-deca-2,7,9-triene.

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